So having a standing wine date with a recruiter was in character for the longtime attorney, and six years ago that relationship landed her at the helm of The Chicago Network.

The Chicago Network, founded in 1979, is an invitation-only group of high-ranking Chicago women whose 450 members span the upper echelons of business, academia, science, the arts and nonprofits.

In the landscape of leadership clubs, Bensen, 57, said the group is distinct for fostering "deep and abiding" relationships among women leaders in disparate circles, operating on the premise that connecting a Fortune 100 CEO with a leading architect will enrich everyone's lives. Criteria for entry are not disclosed, but everyone must demonstrate civic engagement, she said.

Bensen, who became president and CEO in April 2010, did not grow up surrounded by such elite company.

"I came from a household where my mother didn't go to college, my dad (a Lutheran minister) worked his way through a million jobs to put himself through college and seminary," she said.

Before her family moved from a blue-collar neighborhood on Chicago's Northwest Side to Westchester County, N.Y., to care for her ailing grandfather, "I'd never met a wealthy person, I'd never met a corporate executive, I'd never met a Jewish person," Bensen said. "My whole world exploded, and I recognized that my life was never going to be the same."

Bensen credits her rise to recognizing when doors are opening — and in her role, she hopes to open doors for others.

Among the initiatives that have rolled out under her watch are two meant to "cultivate the next generation of women leaders."

One is the Future Leaders program, which invites first-generation female college students at three universities — St. Xavier, the University of Illinois at Chicago and DePaul — to spend two days with the senior management teams at network members' companies, including Ulta Beauty and McDonald's. The other initiative is the annual Launch Pad for Women Senior Leaders conference, which nurtures high-potential women poised to climb the ranks.

The group's annual census, which tracks the progress of women in the boardrooms and executive suites of Chicago's 50 largest public companies, has shown modest gains. The 2014 census (the 2015 report isn't out yet) showed that women held 17.9 percent of director positions and 15.5 percent of executive offices, both improvements over previous years but still a slim share of the pie. The percentage of top female earners fell a bit, to 8.2 percent. At that rate, the report said, women would reach leadership parity in 2079.

Bensen got her undergraduate degree at the University of Chicago, where she studied economics, and her law degree from Loyola University Chicago School of Law. She was a partner at Schiff Harden and later vice president at public affairs firm Conlon Public Strategies (now Conlon and Dunn Public Strategies) before taking the reins of The Chicago Network.

Bensen spoke to the Tribune in The Chicago Network's offices on the Magnificent Mile. The interview has been edited for length and clarity.

Q: How do you view the progress of women in leadership?

A: Glacial. But we're starting to see signs of change. There are CEOs who get it. Miles White at Abbott is a prime example of someone who believes very strongly in the power of diversity to affect the bottom line and the quality of his company. So he holds his managers accountable for performance, and their bonuses are affected if they're not meeting diversity goals. The other factor driving change is institutional investors, at least for public companies. They're calling for greater diversity in senior management and the boards. But really, leadership and culture come from the top, and we need more CEOs who are champions for change.

Q: Why do you think progress has been so slow?

A: I think it's a multifaceted thing. One is that women who step off to raise families have difficulty stepping back on. I think, also, we need to see women taking on more operating roles, going for more profit-and-loss responsibility, because that's really the route to the C-suite. There are also studies on the confidence gap; there are other studies on ambition gaps. And I think they're closely related. But companies have to really adapt for the 21st century. Especially as you look at millennials coming up, their expectations are very different. I think their patience for sitting around, waiting for change is not as great as it might have been for prior generations.

Q: What role do men play in advancing women leaders?

A: The fact that we're now bringing men into the conversation and asking them to be leaders is critically important, and that's how we're going to see change. Most of the women at the top today had men as sponsors. It's important for women to have sponsors who are men and women. And that women sponsor men also. If we're going to see barriers break down, it's that everybody is helping talent succeed.

Q: What is your favorite career advice to give to young people?

A: I have tons!

Q: Pick two.

A: Lean into discomfort, and accept growth opportunities. And asking for what you want is really important. Not in an obnoxious way, but if you don't communicate what you want, people won't know that you want it. A great story about that is Irene Rosenfeld, who runs Mondelez. She was having dinner with her boss, and he said, Irene, what would you like your next move to be. And she said, Hmm, I think I'd like to run a division. A few weeks later, he's having dinner with his boss. Well, the Canadian division opened up. She got that job. She wouldn't have gotten that job had her boss not asked her.

Q: What's the secret to being a good networker without being annoying?

A: Think about it in terms of being a connector, in terms of being helpful to someone. I'm intensely curious. I love meeting people, and I love listening and learning what they do and then just figuring out how I can be helpful. And I never keep track. If you really lead your life that way, you'll find that people think of you and are helpful to you also.

Q: What's a management lesson you've learned?

A: Perfection is the enemy of leadership and happiness. If you're going to move to a leadership position, you need to move beyond that. Recognize that 80 percent is enough; recognize the end goal. There will be people supporting you who have to get that right, but your job as a leader is to step away and make sure the ship is going in the right direction.

Q: What company or executive do you admire most?

A: Globally, I admire Richard Branson the most. I think he is one of the most visionary, creative leaders around who also pays it forward by mentoring entrepreneurs and fostering innovation. Nationally, I would have to say that (Ulta Beauty CEO) Mary Dillon is an inspiration to me. Like me, she grew up in modest circumstances, and what she's doing with Ulta is just amazing. She has a vision, she has the numbers to back it up, and the company's stock price is going through the ceiling.

A version of this article appeared in print on January 17, 2016, in the Business section of the Chicago Tribune with the headline "Networking CEO: `Lean into discomfort' - Her group works to open doors for other women" —
Today's paperToday's paper | Subscribe